(1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

Base Information

Chemical Name:(1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one
CAS No.:564476-53-5
Molecular Formula:C₁₉H₃₄O₃Si
Molecular Weight:338.563
Hs Code.:

Synonyms:(1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

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Chemical Property of (1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

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Technology Process of (1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

There total 7 articles about (1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1067-71-6
Diethyl (2-oxopropyl)phosphonate

: (1R,3S,5S)-3-(tert-butyl(dimethyl)silyloxy)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-ol

: (1R,3S,5S)-[3-(tert-butyl(dimethyl)silyloxy)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]oct-7-yl]acetone

: 564476-53-5
(1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

Guidance literature:: Diethyl (2-oxopropyl)phosphonate; With barium dihydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;

(1R,3S,5S)-3-(tert-butyl(dimethyl)silyloxy)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-ol; In tetrahydrofuran; water; at 20 ℃; for 24h;
DOI:10.1021/jo034424y

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 564476-53-5
(1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 95 percent / i-Bu₂AlH / toluene / -70 °C

3.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

3.2: 204 mg / tetrahydrofuran; H₂O / 24 h / 20 °C

With 1H-imidazole; barium dihydroxide; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034424y

Reference yield:

: 358339-06-7
(1R,5S)-(+)-8,8-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one

: 564476-53-5
(1'R,3'S,5'S)-(3E)-4-(5'-tert-butyl(dimethyl)silyloxy-3'-hydroxy-2',2'-dimethyl-6'-methylenecyclohex-1'-yl)but-3-en-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / SeO₂; t-BuOOH; salicylic acid / CH₂Cl₂; H₂O / 72 h / Heating

2.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 85 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / -18 °C

4.1: 78 percent / imidazole / dimethylformamide / 12 h / 20 °C

5.1: 95 percent / i-Bu₂AlH / toluene / -70 °C

6.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

6.2: 204 mg / tetrahydrofuran; H₂O / 24 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; barium dihydroxide; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; diisobutylaluminium hydride; Dess-Martin periodane; salicylic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo034424y